US4254123AExpiredUtility

Novel imidazoquinoxalines

80
Assignee: ROUSSEL UCLAFPriority: Aug 2, 1978Filed: Jul 30, 1979Granted: Mar 3, 1981
Est. expiryAug 2, 1998(expired)· nominal 20-yr term from priority
Inventors:Peter RammAlan C. Barnes
A61P 37/08A61P 11/00C07D 241/44C07D 487/04
80
PatentIndex Score
16
Cited by
5
References
39
Claims

Abstract

Novel imidazoquinoxalines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, --NH 4 , alkali metal, alkaline earth metal, magnesium, aluminum and non-toxic, pharmaceutically acceptable amines, X is selected from the group consisting of hydrogen, alkoxy of 1 to 5 carbon atoms and carbamoyl and Y and Z are individually selected from the group consisting of hydrogen and halogen and their non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A compound selected from the group consisting of imidazoquinoxalines of the formula ##STR6## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, --NH 4 , alkali metal, alkaline earth metal, magnesium, aluminum and non-toxic, pharmaceutically acceptable amines, X is selected from the group consisting of hydrogen, alkoxy of 1 to 5 carbon atoms and carbamoyl and Y and Z are individually selected from the group consisting of hydrogen and halogen and their non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       2. A compound of claim 1 wherein R is selected from the group consisting of hydrogen and ethyl, X is selected from the group consisting of hydrogen and ethoxy and Y and Z are individually selected from the group consisting of hydrogen and chlorine. 
     
     
       3. A compound of claim 2 wherein R is hydrogen. 
     
     
       4. A compound of claim 1 wherein R, X and Z are hydrogen and Y is selected from the group consisting of hydrogen and chlorine. 
     
     
       5. A compound of claim 1 selected from the group consisting of imidazo-[1,2-a]-quinoxaline-2-carboxylic acid and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       6. A compound of claim 1 selected from the group consisting of ethyl 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylate and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       7. A compound of claim 1 selected from the group consisting of 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       8. A compound of claim 1 selected from the group consisting of 7-chloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       9. A compound of claim 1 selected from the group consisting of 8-chloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       10. A compound of claim 1 selected from the group consisting of 4-ethoxy-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       11. A compound of claim 1 selected from the group consisting of 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       12. A compound of claim 1 which is tri-(hydroxymethyl)methyl-ammonium imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       13. A compound of claim 1 which is sodium imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       14. An antiallergic composition comprising an antiallergically effective amount of at least one compound of claim 1 and an excipient. 
     
     
       15. A composition of claim 14 wherein R is selected from the group consisting of hydrogen and ethyl, X is selected from the group consisting of hydrogen and ethoxy and Y and Z are individually selected from the group consisting of hydrogen and chlorine. 
     
     
       16. A composition of claim 15 wherein R is hydrogen. 
     
     
       17. A composition of claim 14 wherein R, X and Z are hydrogen and Y is hydrogen or chlorine. 
     
     
       18. A composition of claim 14 wherein the compound is selected from the group consisting of imidazo-[1,2-a]-quinoxaline-2-carboxylic acid and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       19. A composition of claim 14 wherein the compound is selected from the group consisting of ethyl 7,8-dichloroimidazo-[1,2-a]-quinoxaline-2-carboxylate, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       20. A composition of claim 14 wherein the compound is selected from the group consisting of 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       21. A composition of claim 14 wherein the compound is selected from the group consisting of 7-chloro-imidazo-1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       22. A composition of claim 14 wherein the compound is selected from the group consisting of 8-chloro-imidazo-1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       23. A composition of claim 14 wherein the compound is selected from the group consisting of 4-ethoxy-imidazo-1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       24. A composition of claim 14 wherein the compound is selected from the group consisting of 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid, and its non-toxic, pharmaceutically acceptable acid addition salts. 
     
     
       25. A composition of claim 14 wherein the compound is tri-(hydroxymethyl)-methyl-ammonium imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       26. A composition of claim 14 wherein the compound is sodium imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       27. A method of relieving allergic symptoms in warm-blooded animals comprising administering to warm-blooded animals an antiallergically effective amount of at least one compound of claim 1. 
     
     
       28. The method of claim 27 wherein R is selected from the group consisting of hydrogen and ethyl, X is selected from the group consisting of hydrogen and ethoxy and Y and Z are individually selected from the group consisting of hydrogen and chlorine. 
     
     
       29. The method of claim 28 wherein R is hydrogen. 
     
     
       30. The method of claim 27 wherein R, X and Z are hydrogen and Y is hydrogen or chlorine. 
     
     
       31. The method of claim 27 wherein the compound is imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       32. The method of claim 27 wherein the compound is ethyl 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       33. The method of claim 27 wherein the compound is 7,8-dichloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       34. The method of claim 27 wherein the compound is 7-chloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       35. The method of claim 27 wherein the compound is 8-chloro-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       36. The method of claim 27 wherein the compound is 4-ethoxy-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       37. The method of claim 27 wherein the compound is 4-carbamoyl-imidazo-[1,2-a]-quinoxaline-2-carboxylic acid. 
     
     
       38. The method of claim 27 wherein the compound is tri-(hydroxymethyl)-methyl-ammonium imidazo-[1,2-a]-quinoxaline-2-carboxylate. 
     
     
       39. The method of claim 27 wherein the compound is sodium imidazo-[1,2-a]-quinoxaline-2-carboxylate.

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